HCID 13829314, compound → HCID 11608251, compound

HRID 1248395Notes

Reaction equation

HRID 1248395 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:10]([O:11][CH3:12])[C@@H:9]([CH2:13][O:14][CH3:15])[O:8][CH:5]([O:6][CH3:7])[C@@H:4]1[OH:16].[CH3:17]O[C@H]1[C@H](O)[C@H](OC)COC1OC>>[CH3:1][O:2][C@H:3]1[C@H:10]([O:11][CH3:12])[C@@H:9]([CH2:13][OH:14])[O:8][CH:5]([O:6][CH3:7])[C@@H:4]1[OH:16].[CH3:17][O:16][C@@H:4]1[C@@H:3]([O:2][CH3:1])[C@H:10]([O:11][CH3:12])[C@@H:9]([CH2:13][O:14][CH3:15])[O:8][CH:5]1[O:6][CH3:7]

Participants

4

Reactant 2

HCID 13829314HCID 13829314, compoundHCID 53768393HCID 53768393, compound

Product 2

HCID 11608251HCID 11608251, compoundHCID 12900881HCID 12900881, compound

Procedure

When it is subjected to methanolysis (i.e., heated under reflux in 9% hydrochloric acid-dry methanol), it gives 1 mol each of methylgalactoside, methylarabinoside and methylglucuronide, and 2 mols of methylglucoside. A completely methylated compound (C77H132O29) obtained by methylation of soyasaponin A1 with methyl iodide, dimethyl sulfoxide and sodium hydride gives 1 mol each of methyl 3,4-di-O -methylglucopyranoside, methyl 3,4,6-tri-O -methylgalactopyranoside and methyl 2,4-di-O-methylarabinopyranoside, and 2 mols of methyl 2,3,4,6-tetra-O-methylglucopyranoside when subjected to methanolysis after reduction. It also gives 1 mol of 3,22,24-tri-O-methyl soyasapogenol A (C33H56O4).

Sources & evidence

ORD record
ord-cf933160d96e4699a6c526daa00f6d97
Source dataset
uspto-grants-1985_06
Patent number
US04524067

Reaction notes

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